


What He Doesn’t Know - (Dean Winchester x Reader)

by deanwanddamons



Category: Supernatural
Genre: Dean Winchester Smut, Dirty Dean Winchester, F/M, Filthy Dean Winchester, Fingering, Sex From Behind, Supernatural - Freeform, dean winchester fanfiction, supernatural fanfiction - Freeform
Language: English
Status: Completed
Published: 2020-04-17
Updated: 2020-04-17
Packaged: 2021-03-01 19:40:20
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,276
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23702476
Author URL: https://archiveofourown.org/users/deanwanddamons/pseuds/deanwanddamons
Summary: You have been living with Sam and Dean for a while now, and you are best friends. But, what Sam doesn’t know is you and Dean have been having a secret relationship for some time.
Relationships: Dean Winchester & You
Kudos: 24





	What He Doesn’t Know - (Dean Winchester x Reader)

Today

“Right guys. I’m going on a supply run,” Sam shouted from the wrought iron stairs leading to the front door of the bunker. 

“Don’t forget the beers,” Dean reminded his brother as he wandered into the room from his bedroom, “And bring me pie,” he added.

“Yes Dean. I’ll get you pie. Y/N?” Sam asked as he leaned over the bannister, directing the question at the young woman sitting at the war room table, “you need anything?” 

“Nachos. And Diet Pepsi,” Y/N replied from her seat, as Dean flopped down next to her. 

“Okay. See you soon” Sam waved as he headed out of the door. 

Dean and Y/N watched Sam leave. After a few seconds of silence he looked at her and lifted one eyebrow. 

“Now’s our chance,” he said with that panty dropping smirk of his. 

“Chance for what?” Y/N responded seductively, licking her lips. 

“This,” Dean answered, pulling her up from her seat as his lips crashed into hers. 

————————————————————————  
Flashback

Y/N had known Sam and Dean Winchester all her life. She was the same age as Sam, four years younger than Dean. Her father was a hunter, and had worked with their father, John, on numerous cases. From a young age she had been involved in the research side of hunting, rather than the physical side. One of the brothers would text or phone her, asking for her advice. Since over the years she’d become quite the expert in lore, particularly where vampires were concerned. 

Three weeks previously, Dean had called and asked for her help. They believed that a nest of vampires had settled in a town not far from Lebanon and were the reason four locals had been killed, drained of blood and their bodies left in the forest. The trouble was that they were struggling to locate them. Agreeing to help, she’d gone to stay with the Winchester’s in the bunker. It was a good opportunity to spend some quality time with the hunters she classed as her best friends. 

She’d had a crush on the elder Winchester for as long as she could remember, but always thought it was unrequited. They used to flirt constantly, Dean would try out his famous pick up lines on her until they would be rolling around the floor laughing, but she’d been convinced that it was just banter. 

Until one evening, when they’d all had a little too much to drink. 

The three of them had started off on the beer, before moving onto Dean’s favourite whiskey. Sam had never been able to match Dean and Y/N drink for drink, so he decided to take himself off to bed after his third whiskey chaser. Which left Dean and Y/N alone, for the first time since she’d got to the bunker. 

After consuming many more whiskies, the talk turned to old cases that they’d worked together, laughing about the scrapes he and Sam had managed to get themselves into, while Y/N had been pouring over the books. The more alcohol they drank, the more animated they became, until Dean had wanted to show Y/N a particular move, one he had used to floor a werewolf. 

Getting up from the chair he pulled Y/N up to her full height, but the whiskey had obviously taken effect on him, because before he could demonstrate any moves, they had both hit the floor. Leaving Dean on top of Y/N as they both laughed hysterically, but when his lips had brushed hers, her laughter died in her throat. 

“Dean. What…?” But she was unable to finish her sentence before he kissed her again. Her lips automatically responded. Lacing her hands behind his neck she pulled him down to her. That was until they heard Sam’s bedroom door open. Quickly regaining their composure, they’d said goodnight and had gone to their separate bedrooms. 

After a slightly awkward exchange the following morning, Dean had managed to get Y/N alone after following her into the bathroom. 

“Can we talk about last night?” he enquired. “Was it just the whiskey, or am I sensing a shift between us?” 

“You tell me Dean. It was you that kissed me after all,” Y/N responded turning to face him. 

“And I want to do it again,” he said as he walked towards her. 

His lips were gentle when they met hers, but the kiss quickly became deep and wanting. Their tongues moved naturally, as if they belonged together. Dean pushed her back against the bathroom sink and dropped down slightly, not breaking the kiss, so that his large hands could reach around the backs of her thighs, lifting her up so she was sitting on the edge. 

Wrapping her legs around his waist, she locked her ankles and pulled his body towards her. Her small hands found the back of his neck, fingertips caressing the soft skin there as the kiss became more passionate. 

“Guys? Where are you? Breakfast is ready!” They heard Sam shout from the kitchen. 

Dean moved away from Y/N so fast, her ass slipped off the sink and her sock clad feet bumped to the ground with a thud. She looked at him, a shocked expression on her face. Dean ran his hands through his hair, his actions clearly agitated. 

“Whatever this is-” Dean said, waving his hand between them, “-Sammy can’t find out.” 

“I don’t even know what this-” Y/N began, mirroring Dean’s gesture, “-is, let alone being able to explain it to anyone else. When we do decide what it is, if it’s anything at all, why can’t Sam know?” she finished with a huff. 

“Sammy’s into you too. Has been for years. He never told me, not until I admitted to him that I’d always had a thing for you ever since we were kids. We made a pact that neither of us would ever make a move,” he turned away, bowing his head as he continued, “I’m ashamed that I broke that pact last night. As you know, I would die for Sammy, so I put it down to the whiskey, but when I saw you this morning,” he took Y/N’s hand in his and took in a deep, shuddering breath, “I realised that it wasn’t just that. I hate the fact that I feel like this and that I’m even considering breaking a promise I made to my brother, but having you here has made me realise. I want you so Goddamn much Y/N. I’m pretty good at reading body language, and you're kinda into me too. Am I right?” His forest green eyes searched her Y/E/C ones. 

“If that kiss didn’t prove it, then your body language skills are as good as your subtlety Winchester,” Y/N replied with a small chuckle, “but I completely get where you’re coming from. You made a promise to Sam, and the last thing I would want to do is hurt him. So if you want to back away from this, then I’m fine with it. I promise there will be no awkwardness from me, but I have had a thing for you for years, Dean, and I will be waiting if you change your mind.” She offered him a small, reassuring smile, a warm blush heating her cheeks as Dean’s intense gaze stayed on her. “We’d better get out of here before Sam comes searching for us,” she told him, clearing her throat as she gripped his shoulders and ushered him towards the door. 

“Guys! Food’s getting cold!” Sam’s voice rang out, echoing around the bunker. 

“Coming!” Y/N called back, as she pushed Dean out of the bathroom, placing the lightest of kisses on his plump lips. “We’ll discuss this later,” she whispered, following him down the corridor towards the kitchen. 

Fast forwarding a few days, Dean and Y/N’s relationship had been going on behind Sam’s back for over a week, not being able to stay away from each other even after discussing how Sam would feel if he knew. Any opportunity they could find, they would sneak a kiss and engage in non verbal flirtatious exchanges. When they were alone in their rooms, they would send each other dirty texts, going into graphic detail what they planned to do to each other when they were able. Sometimes they would go as far as to whisper snippets of their text conversations to each in Sam’s presence, the risk of being discovered making it even more exciting. 

Y/N’s new favourite pastime was to sit opposite the boys while they were doing research. After silently getting Dean’s attention she would open a bottle of beer, and drink it slowly, running her tongue over the top and neck of the bottle, wrapping her lips around it as she poured the liquid into her mouth. Loving the way Dean would watch her, a blush rising up his cheeks, pearly white teeth pulling at his bottom lip, while Sam stayed blissfully unaware.

Dean did appear in Y/N’s room one evening after Sam had gone to bed, climbing into bed with her, and getting under the covers as she watched a movie. This was something she had done numerous times with both him and Sam, but things were different now. 

She had great difficulty resisting his advances as he reminded her in his deep, sexy voice of some of the most explicit text conversations they’d had, while running his fingers up her naked thigh, lightly brushing his thumb along her soaking wet panties. 

Just his presence in her room had made her want to rip his clothes off, there and then. But she’d made him agree that until they were alone in the bunker, things would not go any further than they already had between them, out of respect for Sam's feelings. Knowing Dean as well as she did, Y/N was very surprised he’d agreed to this after she mentioned it to him, but he did, on one condition. 

As soon as Sam left them alone in the bunker, he was going to do to her everything that he had promised in his texts. With a heavy heart, she ushered him out of her bed and out of the room, knowing it wouldn’t be fair on Sam if they went any further while he was around. 

————————————————————————  
Today

“Finally,” Dean groaned against Y/N’s lips, as his calloused hands pushed under her t-shirt. “We don’t know how long Sam’s going to be, so we need to be quick.”

“You’ve been winding me up for so long, Winchester, I just want you to fuck me,” Y/N purred as she fumbled with his belt buckle, popping the button on his jeans. Pulling down the zipper, she pushed them down, so they rested just under his perfect ass. Slipping her hand inside his boxers, she palmed his already hard cock. 

“Fuck,” Dean mumured, as she closed her fist around his erection and slowly started to move her hand up and down. “Good job you’re wearing a skirt,” he said, suddenly spinning her around, so her stomach rested against the edge of the war room table.  
Flattening his hand on the base of her back, he pressed her forward, her ass bumping against his groin. 

She instinctively opened her legs slightly so that he could move his body between them, lifting her hips to meet his pelvis. She took in a deep breath, a whimper escaping her lips, as his hand slid into her panties, pushing two thick fingers inside her wet hole. 

“Wet already?” he growled, his voice a rumble in his chest. She nodded slowly, her forehead coming to rest on the table top. 

“Fuck me Dean, quickly before Sam gets back,” she breathed “I need to have you inside me now!” she almost spat at him. 

Tugging the crotch of her underwear aside, he quickly wriggled his boxers down enough to free his rock hard length. Gripping onto her hips, he lined himself up with her opening, slowly pushing his engorged cock into her soaking pussy. He was a little hesitant at first, afraid that he may hurt her, until he felt her hand reach behind him, gripping at his ass cheek, urging him on. 

His hips jerked forward as he bottomed out, her hand still clutching at his ass. He picked up speed as he pounded into her, her movements matching his pace. One hand holding her hair, pulling her head back, the other hand flat against the edge of the table, using it for leverage. 

Her breathy moans, panting his name, spurred him on, his thrusts getting harder and messier as he felt that familiar feeling rising in the pit of his stomach. The chance of Sam walking in on them made it even more exciting.

The walls of Y/N’s pussy clenched around his cock, milking him, as his name fell from her lips. Her juices were hot and sticky, flooding over him as she came. Dean wasn’t far behind, a deep moan rising from him as he came, coating her pussy with his thick seed. 

“Jesus Christ, Dean. We fucking needed that,” Y/N chuckled as he withdrew from her. She stood up, turning to face him as she adjusted her clothes.

The door to the bunker squeaked open as Sam returned, arms full of groceries. 

“Guys, can you give me a hand?” he shouted down the stairs.

“Shit! That was good timing,” Dean whispered, as he quickly pulled up his jeans. 

“Made it more exciting though, didn’t it?” she grinned. 

“Sure did sweetheart,” he smirked.


End file.
